Things to do in NYC | September 2025
The swimming pools might be closing, but that doesn’t mean summer’s over yet. There are plenty of things happening across the city throughout September – here are our top picks if you want to savor summer for a little longer.

U.S. Open Watch Party with Grey Goose
Sept. 5 | XGolf Williamsburg
Watch the men’s semifinals without the crowds with Grey Goose at XGolf’s watch party. Try specialty cocktails like the Le Grand Slam Fizz, Drop Shot, Match Point, and – obviously – the Honey Deuce. Sick of tennis? The venue’s got golf simulators, pool, and darts, if you want to try something different.

Broadway Week
Sept 8 to 21 | Across Manhattan
If you’ve been putting off seeing that one musical, now’s the time – and you can drag a friend! See some of Broadway's biggest crowd pleasers with 2 for 1 tickets for musicals like Maybe Happy Ending, Mamma Mia, and The Book of Mormon. Now that’s showbiz.

One Bite Pizza Festival
Sept 13 | Randall’s Island
All you can eat pizza is included with every ticket. Do I need to say more? You don’t even need to know the price. Okay, fine – it’s $200. But it’s well worth it, with over 40+ pizzerias from across the country, along with complimentary treats at the Italian Dessert Village. And there’s a Jimmy Buffet Tribute Band. Come on now.

Brooklyn Book Festival
Sept 14 - 22 | Across Brooklyn
The city’s largest free literary festival is back in Brooklyn for its 20th year. Eight days of city-wide events come to a peak on Festival Day on the 21st, with more than 200 local, international, debut, and iconic authors and 200+ publishers filling the Literary Marketplace. It’s a must for bookworms from across the city.

All In Annual Fundraiser
Sept 14 | Union Square Cafe
For the third year in a row, Union Square cafe is partnering with local beloved eateries and bars for a fundraiser. 100% of the proceeds from the $105 tickets go to three local charities: Drive Change, Emma’s Torch, and Food Education Fund. You’ll also get unlimited bites from Crevette, Superiority Burger, Daily Provisions, Mama’s Too, and more, along with cocktails shaken up by Overstory. It’s an opportunity to give back and try some of the most coveted restaurants in the city. Talk about a win-win.

Anne Saxelby Legacy Benefit
Sept 18 | Chelsea Market
Got too many restaurants on your list to try? Believe it or not, you can try all of them in one night for $175 – and it all goes to a good cause. Join 130+ of the city’s top chefs and mixologists for unlimited drinks and bites at the 4th annual Anne Savelby Legacy Fund Benefit. ASLF provides monthlong paid apprenticeships for young adults to live on sustainable farms, investing in community-driven agriculture. Featured restaurants include Gramercy Tavern, Chambers, Gage & Tollner, Carbone, Buddakan, and way, way more.

Matinee Social Club Decade Party
Sept 20 | The Club @ Mr. Purple
Matinee Social Club has been relieving New York’s earlybirds from nightlife FOMO, hosting dance parties and club nights that end at 10pm. Whether you’re a parent or just a bit of a grandma, they offer a way to enjoy themed nights and still be in bed before midnight. The This is 40ish party at Mr. Purple showcases beats from the 80s, 90s, and 00s – ideal for 40-somethings and millennials at heart who want to embrace the nostalgia. Tickets start at $28, and the party starts at 6. Phew.

NYC Bakery Run
Sept 21 | La Cabra, Bushwick
Ideal for anyone who only exercises when they’ve got a reward (me), Tipster’s first-ever NYC Bakery Run is a half-marathon fueled by pastries made by some of the city’s best bakeries. If you’ve got a knack for treats and you’re regretting signing up for the NYC marathon, this is a good way to add a bit of sweetness to your training. Eight bakeries are taking part, including L’Appartement 4F, Elbow Bread, and Librae Bakery. 100 runners will be chosen via lottery (enter by Sept. 10) – and all the treats are free.

All Things Go
Sept 26 to 28 | Forest Hills Stadium
NYC’s favorite indie girl convention is back. See Clairo, The Marias, Doechii, Lucy Dacus, and more at Forest Hills Stadium, with tickets starting at $90 for a day pass and $205 for a 3-day. This festival is particularly unique because there’s no overlapping sets, so you can see all of your favorites without missing a beat.
Looking for more things to see, eat, and drink in NYC? Check us out on Instagram @headboxnyc.
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